I think I saw it as pretty cool to fly everywhere and get free flight benefits (most of our trips growing up were in the family station wagon). Plus my friends' dads had time off when they weren't flying. It seemed awesome

I think part of the gap is not only because of expectation, but because the nature of the profession changes over time as well. Those kinds of jobs where you keep on moving up and the senior pilots get to do international long haul on a major carrier and get all sorts of benefits simply don't exist anymore.